New water insoluble azodyestuffs



Patented June 7, 1932 FP-NI EP-iS PATENT/OFFICE LEOPOLD LASKA AND ARTHURZITSCHER, OF OFFENBACH-ON-THE-MAIN, GERMANY, AS-

SIGNORS TO GENERAL AN ILIN E WORKS, IN 0., OF NEW YORK, N. Y., ACORPORATION OF DELAWARE NEW WATER INSOLUIBLE nzonyns'rurrs No Drawing.Application filed August 27, 1929, Serial No. {388,850, and in GermanySeptember; 1928.-

The present invention relates to new waterinsoluble azodyestufiscorresponding probably to the general formula:

wherein aryl means the residue of an aromatic diazo-, tetrazoordiaz'o-azo-compound not containing a solubilizing group such as asulfonic or carboxylic acid group.

The new azodyestufis are obtained by combining either in substance or onthe fiber an aromatic diazo-, tetrazoor diazo-azo-compound of theaforesaid land with 2 3-hydroXynaphthoyl-L-amino-aoenaphthene.

2 3"-hydroxynaphthoyl-1-naphthylamine the present dyestuffs aredistinguished by an extraordinarily dark shade of the lakes, dye-Compared with the dyestuifs derived from ings and printings obtainabletherewith.

Even when using the diazo-oompounds of relatively simple bases for thecombination, dark garnet and claret-red shades are obtained, which areof a special value for many kinds of I application. Furthermore somedyestuffs of the present series yield dyeings Example Well boiled anddried cotton yarn is im- 1 pregnated with a solution of 5.5 grs. of 2 3-hydroxynaphthoyl 4 amino acenaphthene, 13 com. of a caustic sodasolution of 34 B., 10 com. of Turkey red oil in the liter, well wrungout and developed in a diazosolution neutralized with sodium acetate andcontaining per liter 1.4 grs. of Q-nitro-aniline, rinsed and soaped.

A brown garnet-like dyeing of a good fasta OH NO: j

-o o-NH- om -When using'in the same manner the wdiazo com-- pound of: p2:5-dich1oro-aniline the following shades are obtained:

orange-brown 2t4 -dichloro-aniline full claret 3-n1tro-1.4to1uidine darkclaret 5-nitro-2-to1uidine bluish garnet 4nit'ro-2.-anisidine claret3-nitl'o-lA-ani sidine l-amino-anthraquinone dianisidine (subsequentlytreated with copper) dark blue 7 I o-am1no-azotoluene dark bluishviolet-red 5-ch1oro-2-toluidine full-bluish 1'ed Since anob ect of thepresent lnvent on 1s to provide dyestuffs of good fastness properties,whlch dyestuifs are insoluble in water and alkalles, 1t ls'to beunderstoodethat" the aromatlc nuclei, of the general formulae appearing1n the appended cla ms contain no substltuentswhich are known to. renderorganlo compounds soluble in. water orialkalies and .to tendtodepreciate the fastness of-the dyestuffs to alkalles. 'Substituents ofthis kind are the sulfomc acid, the carboxylicacid and the hydroxygroup.

We claim 1. As new compounds water-insoluble azodark violet-redbrownishgarnet dyestuffs corresponding probably to the general formulaable therewith;

2. As new compounds water-insoluble azowhich dyestufi yields bluishgarnet color dyestuffs corresponding probably to the genlakes anddyeings.

eral formula:

wherein the benzene nucleus may contain an alkyl or alkoxy group whichdyestuffs are distinguished by the dark garnetto claretred shades of thecolor lakes, dyeings and printings obtainable therewith.

' 3; As new compounds water-insoluble azodyestuffs correspondingprobably to the general formula:

--CONH -oi1, V I i tin wherein X means hydrogen, methyl or methoxy,which dyestuffs are distinguished by In testimony whereof, we afiix oursignatures.

the dark garnetto claret-red shades of the Y color lakes, dyeings andprintings obtainable therewith.

4. As a new compound the water insoluble azodyestufi correspondingprobably to the formula formula OCHI 7 which dyestuff yields dark claretcolor lakes and dyeings. V y

6. Asa new compound, the water-insoluble azodyestuff correspondingprobably to the c formula LEOPOLD LASKA. ARTHUR ZITSCHER.

